Iodoethane → (alphaS)-3-ethyl-3-(mercaptomethyl)-alpha-methyl-2-oxo-1-pyrrolidineacetic acid

HRID 1583568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1583568
[CH3:1][C@H:2]([N:6]1CCC[C:7]1=[O:11])[C:3]([OH:5])=[O:4].C(I)C.[CH2:15]([S:22]CBr)[C:16]1[CH:21]=[CH:20]C=[CH:18][CH:17]=1>>[CH2:21]([C:16]1([CH2:15][SH:22])[CH2:17][CH2:18][N:6]([C@@H:2]([CH3:1])[C:3]([OH:5])=[O:4])[C:7]1=[O:11])[CH3:20]

Komponenten

4

Edukt 3

HCID 6340IodoethaneHCID 4067177BenzylthiobromomethaneHCID 7175678(S)-2-(2-oxopyrrolidin-1-yl)propanoic acid

Produkt 1

HCID 18600216(alphaS)-3-ethyl-3-(mercaptomethyl)-alpha-methyl-2-oxo-1-pyrrolidineacetic acid

Versuchsvorschrift

Following the procedures of Examples 1C-1E, α(S)-methyl-2-oxo-1-pyrrolidineacetic acid was first alkylated with ethyl iodide and then with benzylmercaptomethyl bromide. Removal of the benzyl group in the usual way and purification by chromatography provided the title compound as a mixture of diastereomers. [α]D25 =-4.04° (c=1, methanol).

Aufarbeitung

  1. customRemoval of the benzyl group
  2. customin the usual way and purification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f5282b269af4496fb176721b5249d416
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04552889

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